HCID 136340649, compound → HCID 136340651, compound

HRID 920488Notes

Reaction equation

HRID 920488 reaction equation
[CH3:1][N:2]([CH3:41])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[CH:11]=[C:10]3[NH:15][C:16]([C:18]4[C:19](=[O:38])[NH:20][CH:21]=[CH:22][C:23]=4[NH:24][CH:25]([CH3:37])[CH2:26][C:27]4[C:32]([F:33])=[C:31]([F:34])[CH:30]=[C:29]([F:35])[C:28]=4[F:36])=[N:17][C:9]3=[C:8]([CH3:39])[C:7]=2[C:6]1=O>[Zn].C(O)(=O)C>[CH3:41][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[CH2:6][C:7]2[C:8]([CH3:39])=[C:9]3[N:17]=[C:16]([C:18]4[C:19](=[O:38])[NH:20][CH:21]=[CH:22][C:23]=4[NH:24][CH:25]([CH3:37])[CH2:26][C:27]4[C:28]([F:36])=[C:29]([F:35])[CH:30]=[C:31]([F:34])[C:32]=4[F:33])[NH:15][C:10]3=[CH:11][C:12]=2[C:13]1=[O:14]

Participants

4

Reactant 1

HCID 136340649HCID 136340649, compound

Product 1

HCID 136340651HCID 136340651, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 6-(2-(dimethylamino)ethyl)-4-methyl-2-(2-oxo-4-(1-(2,3,5,6-tetrafluorophenyl)propan-2-ylamino)-1,2-dihydropyridin-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.25 g, 0.44 mmol), zinc dust (0.29 g, 4.38 mmol), and 7.5 mL of acetic acid was heated at reflux for 13-14 h under an argon atmosphere. Product was separated by a silica gel column using methylene chloride and methanol (85:15 v/v) as eluent to afford 30 mg of the designed compound as yellowish solid. 1H NMR (500 MHz, DMSO-d6) δ 12.93 (s, 1H, NH), 11.28 (d, J=8.5 Hz, 1H, NH), 11.27 (s, 1H, NH), 7.78-7.74 (m, 1H, ArH), 7.59 (s, 1H, ArH), 7.37 (d, J=7.5 Hz, 1H, ArH), 6.20 (d, J=7.5 Hz, 1H, ArH), 4.46 (s, 2H, CH2), 4.30-4.27 (m, 1H, CH), 3.60-3.57 (m, 2H, CH2), 3.08-3.06 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.19 (s, 6H, 2×CH3), 1.83 (s, 3H, CH3), 1.36 (d, J=6.5 Hz, 3H, CH3); Mass (ESI, positive) m/z 557.2 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 13-14 h under an argon atmosphere
  3. customProduct was separated by a silica gel column

Sources & evidence

ORD record
ord-72424dc51f34457a98d62d17c1cc5a97
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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